class TestToolkitRegistry:
"""Test the ToolkitRegistry"""
@pytest.mark.skipif(not OpenEyeToolkitWrapper.is_available(),
reason='OpenEye Toolkit not available')
def test_register_openeye(self):
"""Test creation of toolkit registry with OpenEye toolkit"""
# Test registration of OpenEyeToolkitWrapper
toolkit_precedence = [OpenEyeToolkitWrapper]
registry = ToolkitRegistry(toolkit_precedence=toolkit_precedence,
register_imported_toolkit_wrappers=False)
#registry.register_toolkit(OpenEyeToolkitWrapper)
assert set([type(c) for c in registry.registered_toolkits
]) == set([OpenEyeToolkitWrapper])
# Test ToolkitRegistry.resolve()
assert registry.resolve(
'to_smiles') == registry.registered_toolkits[0].to_smiles
# Test ToolkitRegistry.call()
smiles = '[H]C([H])([H])C([H])([H])[H]'
molecule = registry.call('from_smiles', smiles)
smiles2 = registry.call('to_smiles', molecule)
assert smiles == smiles2
@pytest.mark.skipif(not RDKitToolkitWrapper.is_available(),
reason='RDKit Toolkit not available')
def test_register_rdkit(self):
"""Test creation of toolkit registry with RDKit toolkit"""
# Test registration of RDKitToolkitWrapper
toolkit_precedence = [RDKitToolkitWrapper]
registry = ToolkitRegistry(toolkit_precedence=toolkit_precedence,
register_imported_toolkit_wrappers=False)
#registry.register_toolkit(RDKitToolkitWrapper)
assert set([type(c) for c in registry.registered_toolkits
]) == set([RDKitToolkitWrapper])
# Test ToolkitRegistry.resolve()
assert registry.resolve(
'to_smiles') == registry.registered_toolkits[0].to_smiles
# Test ToolkitRegistry.call()
smiles = '[H][C]([H])([H])[C]([H])([H])[H]'
molecule = registry.call('from_smiles', smiles)
smiles2 = registry.call('to_smiles', molecule)
assert smiles == smiles2
@pytest.mark.skipif(
not RDKitToolkitWrapper.is_available()
or not AmberToolsToolkitWrapper.is_available(),
reason='RDKitToolkit and AmberToolsToolkit not available')
def test_register_ambertools(self):
"""Test creation of toolkit registry with AmberToolsToolkitWrapper and RDKitToolkitWrapper
"""
# Test registration of AmberToolsToolkitWrapper
toolkit_precedence = [AmberToolsToolkitWrapper, RDKitToolkitWrapper]
registry = ToolkitRegistry(toolkit_precedence=toolkit_precedence,
register_imported_toolkit_wrappers=False)
#registry.register_toolkit(AmberToolsToolkitWrapper)
assert set([type(c) for c in registry.registered_toolkits
]) == set([AmberToolsToolkitWrapper, RDKitToolkitWrapper])
# Test ToolkitRegistry.resolve()
registry.resolve('compute_partial_charges')
assert registry.resolve(
'compute_partial_charges'
) == registry.registered_toolkits[0].compute_partial_charges
# Test ToolkitRegistry.call()
registry.register_toolkit(RDKitToolkitWrapper)
smiles = '[H]C([H])([H])C([H])([H])[H]'
molecule = registry.call('from_smiles', smiles)
class TestOpenEyeToolkitWrapper:
"""Test the OpenEyeToolkitWrapper"""
# TODO: Make separate smiles_add_H and smiles_explicit_H tests
@pytest.mark.skipif(not OpenEyeToolkitWrapper.is_available(),
reason='OpenEye Toolkit not available')
def test_smiles(self):
"""Test OpenEyeToolkitWrapper to_smiles() and from_smiles()"""
toolkit_wrapper = OpenEyeToolkitWrapper()
# This differs from RDKit's SMILES due to different canonicalization schemes
smiles = '[H]C([H])([H])C([H])([H])[H]'
molecule = Molecule.from_smiles(smiles,
toolkit_registry=toolkit_wrapper)
smiles2 = molecule.to_smiles(toolkit_registry=toolkit_wrapper)
assert smiles == smiles2
@pytest.mark.skipif(not OpenEyeToolkitWrapper.is_available(),
reason='OpenEye Toolkit not available')
def test_smiles_missing_stereochemistry(self):
"""Test OpenEyeToolkitWrapper to_smiles() and from_smiles()"""
toolkit_wrapper = OpenEyeToolkitWrapper()
unspec_chiral_smiles = r"C\C(F)=C(/F)CC(C)(Cl)Br"
spec_chiral_smiles = r"C\C(F)=C(/F)C[C@@](C)(Cl)Br"
unspec_db_smiles = r"CC(F)=C(F)C[C@@](C)(Cl)Br"
spec_db_smiles = r"C\C(F)=C(/F)C[C@@](C)(Cl)Br"
for title, smiles, raises_exception in [
("unspec_chiral_smiles", unspec_chiral_smiles, True),
("spec_chiral_smiles", spec_chiral_smiles, False),
("unspec_db_smiles", unspec_db_smiles, True),
("spec_db_smiles", spec_db_smiles, False),
]:
if raises_exception:
with pytest.raises(UndefinedStereochemistryError) as context:
Molecule.from_smiles(smiles,
toolkit_registry=toolkit_wrapper)
Molecule.from_smiles(smiles,
toolkit_registry=toolkit_wrapper,
allow_undefined_stereo=True)
else:
Molecule.from_smiles(smiles, toolkit_registry=toolkit_wrapper)
# TODO: test_smiles_round_trip
@pytest.mark.skipif(not OpenEyeToolkitWrapper.is_available(),
reason='OpenEye Toolkit not available')
def test_smiles_add_H(self):
"""Test OpenEyeToolkitWrapper for adding explicit hydrogens"""
toolkit_wrapper = OpenEyeToolkitWrapper()
# This differs from RDKit's SMILES due to different canonicalization schemes
input_smiles = 'CC'
expected_output_smiles = '[H]C([H])([H])C([H])([H])[H]'
molecule = Molecule.from_smiles(input_smiles,
toolkit_registry=toolkit_wrapper)
smiles2 = molecule.to_smiles(toolkit_registry=toolkit_wrapper)
assert expected_output_smiles == smiles2
@pytest.mark.skipif(not OpenEyeToolkitWrapper.is_available(),
reason='OpenEye Toolkit not available')
def test_smiles_charged(self):
"""Test OpenEyeToolkitWrapper functions for reading/writing charged SMILES"""
toolkit_wrapper = OpenEyeToolkitWrapper()
# This differs from RDKit's expected output due to different canonicalization schemes
smiles = '[H]C([H])([H])[N+]([H])([H])[H]'
molecule = Molecule.from_smiles(smiles,
toolkit_registry=toolkit_wrapper)
smiles2 = molecule.to_smiles(toolkit_registry=toolkit_wrapper)
assert smiles == smiles2
@pytest.mark.skipif(not OpenEyeToolkitWrapper.is_available(),
reason='OpenEye Toolkit not available')
def test_to_from_openeye_core_props_filled(self):
"""Test OpenEyeToolkitWrapper to_openeye() and from_openeye()"""
toolkit_wrapper = OpenEyeToolkitWrapper()
# Replacing with a simple molecule with stereochemistry
input_smiles = r'C\C(F)=C(/F)C[C@@](C)(Cl)Br'
expected_output_smiles = r'[H]C([H])([H])/C(=C(/C([H])([H])[C@@](C([H])([H])[H])(Cl)Br)\F)/F'
molecule = Molecule.from_smiles(input_smiles,
toolkit_registry=toolkit_wrapper)
assert molecule.to_smiles(
toolkit_registry=toolkit_wrapper) == expected_output_smiles
# Populate core molecule property fields
molecule.name = 'Alice'
partial_charges = unit.Quantity(
np.array([
-.9, -.8, -.7, -.6, -.5, -.4, -.3, -.2, -.1, 0., .1, .2, .3,
.4, .5, .6, .7, .8
]), unit.elementary_charge)
molecule.partial_charges = partial_charges
coords = unit.Quantity(
np.array([['0.0', '1.0', '2.0'], ['3.0', '4.0', '5.0'],
['6.0', '7.0', '8.0'], ['9.0', '10.0', '11.0'],
['12.0', '13.0', '14.0'], ['15.0', '16.0', '17.0'],
['18.0', '19.0', '20.0'], ['21.0', '22.0', '23.0'],
['24.0', '25.0', '26.0'], ['27.0', '28.0', '29.0'],
['30.0', '31.0', '32.0'], ['33.0', '34.0', '35.0'],
['36.0', '37.0', '38.0'], ['39.0', '40.0', '41.0'],
['42.0', '43.0', '44.0'], ['45.0', '46.0', '47.0'],
['48.0', '49.0', '50.0'], ['51.0', '52.0', '53.0']]),
unit.angstrom)
molecule.add_conformer(coords)
# Populate core atom property fields
molecule.atoms[2].name = 'Bob'
# Ensure one atom has its stereochemistry specified
central_carbon_stereo_specified = False
for atom in molecule.atoms:
if (atom.atomic_number == 6) and atom.stereochemistry == "S":
central_carbon_stereo_specified = True
assert central_carbon_stereo_specified
# Populate bond core property fields
fractional_bond_orders = [float(val) for val in range(1, 19)]
for fbo, bond in zip(fractional_bond_orders, molecule.bonds):
bond.fractional_bond_order = fbo
# Do a first conversion to/from oemol
oemol = molecule.to_openeye()
molecule2 = Molecule.from_openeye(oemol)
# Test that properties survived first conversion
# assert molecule.to_dict() == molecule2.to_dict()
assert molecule.name == molecule2.name
# NOTE: This expects the same indexing scheme in the original and new molecule
central_carbon_stereo_specified = False
for atom in molecule2.atoms:
if (atom.atomic_number == 6) and atom.stereochemistry == "S":
central_carbon_stereo_specified = True
assert central_carbon_stereo_specified
for atom1, atom2 in zip(molecule.atoms, molecule2.atoms):
assert atom1.to_dict() == atom2.to_dict()
for bond1, bond2 in zip(molecule.bonds, molecule2.bonds):
assert bond1.to_dict() == bond2.to_dict()
assert (molecule._conformers[0] == molecule2._conformers[0]).all()
for pc1, pc2 in zip(molecule._partial_charges,
molecule2._partial_charges):
pc1_ul = pc1 / unit.elementary_charge
pc2_ul = pc2 / unit.elementary_charge
assert_almost_equal(pc1_ul, pc2_ul, decimal=6)
assert molecule2.to_smiles(
toolkit_registry=toolkit_wrapper) == expected_output_smiles
@pytest.mark.skipif(not OpenEyeToolkitWrapper.is_available(),
reason='OpenEye Toolkit not available')
def test_to_from_openeye_core_props_unset(self):
"""Test OpenEyeToolkitWrapper to_openeye() and from_openeye() when given empty core property fields"""
toolkit_wrapper = OpenEyeToolkitWrapper()
# Using a simple molecule with tetrahedral and bond stereochemistry
input_smiles = r'C\C(F)=C(/F)C[C@](C)(Cl)Br'
expected_output_smiles = r'[H]C([H])([H])/C(=C(/C([H])([H])[C@](C([H])([H])[H])(Cl)Br)\F)/F'
molecule = Molecule.from_smiles(input_smiles,
toolkit_registry=toolkit_wrapper)
assert molecule.to_smiles(
toolkit_registry=toolkit_wrapper) == expected_output_smiles
# Ensure one atom has its stereochemistry specified
central_carbon_stereo_specified = False
for atom in molecule.atoms:
if (atom.atomic_number == 6) and atom.stereochemistry == "R":
central_carbon_stereo_specified = True
assert central_carbon_stereo_specified
# Do a first conversion to/from oemol
rdmol = molecule.to_openeye()
molecule2 = Molecule.from_openeye(rdmol)
# Test that properties survived first conversion
assert molecule.name == molecule2.name
# NOTE: This expects the same indexing scheme in the original and new molecule
central_carbon_stereo_specified = False
for atom in molecule2.atoms:
if (atom.atomic_number == 6) and atom.stereochemistry == "R":
central_carbon_stereo_specified = True
assert central_carbon_stereo_specified
for atom1, atom2 in zip(molecule.atoms, molecule2.atoms):
assert atom1.to_dict() == atom2.to_dict()
for bond1, bond2 in zip(molecule.bonds, molecule2.bonds):
assert bond1.to_dict() == bond2.to_dict()
assert (molecule._conformers == None)
assert (molecule2._conformers == None)
for pc1, pc2 in zip(molecule._partial_charges,
molecule2._partial_charges):
pc1_ul = pc1 / unit.elementary_charge
pc2_ul = pc2 / unit.elementary_charge
assert_almost_equal(pc1_ul, pc2_ul, decimal=6)
assert molecule2.to_smiles(
toolkit_registry=toolkit_wrapper) == expected_output_smiles
@pytest.mark.skipif(not OpenEyeToolkitWrapper.is_available(),
reason='OpenEye Toolkit not available')
def test_from_openeye_implicit_hydrogen(self):
"""
Test OpenEyeToolkitWrapper for loading a molecule with implicit
hydrogens (correct behavior is to add them explicitly)
"""
from openeye import oechem
smiles_impl = "C#C"
oemol_impl = oechem.OEMol()
oechem.OESmilesToMol(oemol_impl, smiles_impl)
molecule_from_impl = Molecule.from_openeye(oemol_impl)
assert molecule_from_impl.n_atoms == 4
smiles_expl = "HC#CH"
oemol_expl = oechem.OEMol()
oechem.OESmilesToMol(oemol_expl, smiles_expl)
molecule_from_expl = Molecule.from_openeye(oemol_expl)
assert molecule_from_expl.to_smiles() == molecule_from_impl.to_smiles()
@pytest.mark.skipif(not OpenEyeToolkitWrapper.is_available(),
reason='OpenEye Toolkit not available')
def test_openeye_from_smiles_hydrogens_are_explicit(self):
"""
Test to ensure that OpenEyeToolkitWrapper.from_smiles has the proper behavior with
respect to its hydrogens_are_explicit kwarg
"""
toolkit_wrapper = OpenEyeToolkitWrapper()
smiles_impl = "C#C"
with pytest.raises(
ValueError,
match=
"but OpenEye Toolkit interpreted SMILES 'C#C' as having implicit hydrogen"
) as excinfo:
offmol = Molecule.from_smiles(smiles_impl,
toolkit_registry=toolkit_wrapper,
hydrogens_are_explicit=True)
offmol = Molecule.from_smiles(smiles_impl,
toolkit_registry=toolkit_wrapper,
hydrogens_are_explicit=False)
assert offmol.n_atoms == 4
smiles_expl = "HC#CH"
offmol = Molecule.from_smiles(smiles_expl,
toolkit_registry=toolkit_wrapper,
hydrogens_are_explicit=True)
assert offmol.n_atoms == 4
# It's debatable whether this next function should pass. Strictly speaking, the hydrogens in this SMILES
# _are_ explicit, so allowing "hydrogens_are_explicit=False" through here is allowing a contradiction.
# We might rethink the name of this kwarg.
offmol = Molecule.from_smiles(smiles_expl,
toolkit_registry=toolkit_wrapper,
hydrogens_are_explicit=False)
assert offmol.n_atoms == 4
@pytest.mark.skipif(not OpenEyeToolkitWrapper.is_available(),
reason='OpenEye Toolkit not available')
def test_get_sdf_coordinates(self):
"""Test OpenEyeToolkitWrapper for importing a single set of coordinates from a sdf file"""
toolkit_wrapper = OpenEyeToolkitWrapper()
filename = get_data_file_path('molecules/toluene.sdf')
molecule = Molecule.from_file(filename,
toolkit_registry=toolkit_wrapper)
assert len(molecule._conformers) == 1
assert molecule._conformers[0].shape == (15, 3)
@pytest.mark.skipif(not OpenEyeToolkitWrapper.is_available(),
reason='OpenEye Toolkit not available')
@pytest.mark.skip
def test_get_multiconformer_sdf_coordinates(self):
"""Test OpenEyeToolkitWrapper for importing multiple sets of coordinates from a sdf file"""
raise NotImplementedError
toolkit_wrapper = OpenEyeToolkitWrapper()
filename = get_data_file_path('molecules/toluene.sdf')
molecule = Molecule.from_file(filename,
toolkit_registry=toolkit_wrapper)
assert len(molecule._conformers) == 1
assert molecule._conformers[0].shape == (15, 3)
@pytest.mark.skipif(not OpenEyeToolkitWrapper.is_available(),
reason='OpenEye Toolkit not available')
def test_get_mol2_coordinates(self):
"""Test OpenEyeToolkitWrapper for importing a single set of molecule coordinates"""
toolkit_wrapper = OpenEyeToolkitWrapper()
filename = get_data_file_path('molecules/toluene.mol2')
molecule1 = Molecule.from_file(filename,
toolkit_registry=toolkit_wrapper)
assert len(molecule1._conformers) == 1
assert molecule1._conformers[0].shape == (15, 3)
assert_almost_equal(molecule1.conformers[0][5][1] / unit.angstrom,
22.98,
decimal=2)
# Test loading from file-like object
with open(filename, 'r') as infile:
molecule2 = Molecule(infile,
file_format='MOL2',
toolkit_registry=toolkit_wrapper)
assert molecule1.is_isomorphic(molecule2)
assert len(molecule2._conformers) == 1
assert molecule2._conformers[0].shape == (15, 3)
assert_almost_equal(molecule2.conformers[0][5][1] / unit.angstrom,
22.98,
decimal=2)
# Test loading from gzipped mol2
import gzip
with gzip.GzipFile(filename + '.gz', 'r') as infile:
molecule3 = Molecule(infile,
file_format='MOL2',
toolkit_registry=toolkit_wrapper)
assert molecule1.is_isomorphic(molecule3)
assert len(molecule3._conformers) == 1
assert molecule3._conformers[0].shape == (15, 3)
assert_almost_equal(molecule3.conformers[0][5][1] / unit.angstrom,
22.98,
decimal=2)
@pytest.mark.skipif(not OpenEyeToolkitWrapper.is_available(),
reason='OpenEye Toolkit not available')
def test_get_mol2_charges(self):
"""Test OpenEyeToolkitWrapper for importing a mol2 file specifying partial charges"""
toolkit_wrapper = OpenEyeToolkitWrapper()
filename = get_data_file_path('molecules/toluene_charged.mol2')
molecule = Molecule.from_file(filename,
toolkit_registry=toolkit_wrapper)
assert len(molecule._conformers) == 1
assert molecule._conformers[0].shape == (15, 3)
target_charges = unit.Quantity(
np.array([
-0.1342, -0.1271, -0.1271, -0.1310, -0.1310, -0.0765, -0.0541,
0.1314, 0.1286, 0.1286, 0.1303, 0.1303, 0.0440, 0.0440, 0.0440
]), unit.elementary_charge)
for pc1, pc2 in zip(molecule._partial_charges, target_charges):
pc1_ul = pc1 / unit.elementary_charge
pc2_ul = pc2 / unit.elementary_charge
assert_almost_equal(pc1_ul, pc2_ul, decimal=4)
@pytest.mark.skipif(not OpenEyeToolkitWrapper.is_available(),
reason='OpenEye Toolkit not available')
def test_get_mol2_gaff_atom_types(self):
"""Test that a warning is raised OpenEyeToolkitWrapper when it detects GAFF atom types in a mol2 file."""
toolkit_wrapper = OpenEyeToolkitWrapper()
mol2_file_path = get_data_file_path(
'molecules/AlkEthOH_test_filt1_ff.mol2')
with pytest.warns(GAFFAtomTypeWarning, match='SYBYL'):
Molecule.from_file(mol2_file_path,
toolkit_registry=toolkit_wrapper)
@pytest.mark.skipif(not OpenEyeToolkitWrapper.is_available(),
reason='OpenEye Toolkit not available')
def test_generate_conformers(self):
"""Test OpenEyeToolkitWrapper generate_conformers()"""
toolkit_wrapper = OpenEyeToolkitWrapper()
smiles = '[H]C([H])([H])C([H])([H])[H]'
molecule = toolkit_wrapper.from_smiles(smiles)
molecule.generate_conformers()
assert molecule.n_conformers != 0
assert not (molecule.conformers[0] == (0. * unit.angstrom)).all()
# TODO: Make this test more robust
@pytest.mark.skipif(not OpenEyeToolkitWrapper.is_available(),
reason='OpenEye Toolkit not available')
def test_compute_partial_charges(self):
"""Test OpenEyeToolkitWrapper compute_partial_charges()"""
toolkit_wrapper = OpenEyeToolkitWrapper()
smiles = '[H]C([H])([H])C([H])([H])[H]'
molecule = toolkit_wrapper.from_smiles(smiles)
# Ensure that an exception is raised if no conformers are provided
with pytest.raises(Exception) as excinfo:
molecule.compute_partial_charges(toolkit_registry=toolkit_wrapper)
molecule.generate_conformers(toolkit_registry=toolkit_wrapper)
# Ensure that an exception is raised if an invalid charge model is passed in
with pytest.raises(Exception) as excinfo:
charge_model = 'notARealChargeModel'
molecule.compute_partial_charges(toolkit_registry=toolkit_wrapper,
charge_model=charge_model)
# TODO: Test all supported charge models
# Note: "amber" and "amberff94" only work for a subset of residue types, so we'll need to find testing data for
# those
# charge_model = [,'amber','amberff94']
# TODO: 'mmff' and 'mmff94' often assign charges of 0, presumably if the molecule is unrecognized.
# charge_model = ['mmff', 'mmff94']
for charge_model in [
'noop', 'am1bcc', 'am1bccnosymspt', 'am1bccelf10'
]:
with pytest.raises(NotImplementedError) as excinfo:
molecule.compute_partial_charges(
toolkit_registry=toolkit_wrapper
) # , charge_model=charge_model)
charge_sum = 0 * unit.elementary_charge
for pc in molecule._partial_charges:
charge_sum += pc
assert charge_sum < 0.001 * unit.elementary_charge
# For now, just test AM1-BCC while the SMIRNOFF spec for other charge models gets worked out
molecule.compute_partial_charges_am1bcc(
toolkit_registry=toolkit_wrapper) # , charge_model=charge_model)
charge_sum = 0 * unit.elementary_charge
for pc in molecule._partial_charges:
charge_sum += pc
assert charge_sum < 0.001 * unit.elementary_charge
@pytest.mark.skipif(not OpenEyeToolkitWrapper.is_available(),
reason='OpenEye Toolkit not available')
def test_compute_partial_charges_net_charge(self):
"""Test OpenEyeToolkitWrapper compute_partial_charges() on a molecule with a net +1 charge"""
toolkit_wrapper = OpenEyeToolkitWrapper()
smiles = '[H]C([H])([H])[N+]([H])([H])[H]'
molecule = toolkit_wrapper.from_smiles(smiles)
molecule.generate_conformers(toolkit_registry=toolkit_wrapper)
with pytest.raises(NotImplementedError) as excinfo:
charge_model = 'notARealChargeModel'
molecule.compute_partial_charges(toolkit_registry=toolkit_wrapper
) #, charge_model=charge_model)
# TODO: Test all supported charge models
# TODO: "amber" and "amberff94" only work for a subset of residue types, so we'll need to find testing data for
# those
# charge_model = [,'amber','amberff94']
# The 'noop' charge model doesn't add up to the formal charge, so we shouldn't test it
# charge_model = ['noop']
for charge_model in [
'mmff', 'mmff94', 'am1bcc', 'am1bccnosymspt', 'am1bccelf10'
]:
with pytest.raises(NotImplementedError) as excinfo:
molecule.compute_partial_charges(
toolkit_registry=toolkit_wrapper
) #, charge_model=charge_model)
charge_sum = 0 * unit.elementary_charge
for pc in molecule._partial_charges:
charge_sum += pc
assert 0.999 * unit.elementary_charge < charge_sum < 1.001 * unit.elementary_charge
# For now, I'm just testing AM1-BCC (will test more when the SMIRNOFF spec for other charges is finalized)
molecule.compute_partial_charges_am1bcc(
toolkit_registry=toolkit_wrapper)
charge_sum = 0 * unit.elementary_charge
for pc in molecule._partial_charges:
charge_sum += pc
assert 0.999 * unit.elementary_charge < charge_sum < 1.001 * unit.elementary_charge
@pytest.mark.skipif(not OpenEyeToolkitWrapper.is_available(),
reason='OpenEye Toolkit not available')
def test_compute_partial_charges_trans_cooh_am1bcc(self):
"""Test OpenEyeToolkitWrapper for computing partial charges for problematic molecules, as exemplified by
Issue 346 (https://github.com/openforcefield/openforcefield/issues/346)"""
lysine = Molecule.from_smiles("C(CC[NH3+])C[C@@H](C(=O)O)N")
toolkit_wrapper = OpenEyeToolkitWrapper()
lysine.generate_conformers(toolkit_registry=toolkit_wrapper)
lysine.compute_partial_charges_am1bcc(toolkit_registry=toolkit_wrapper)
@pytest.mark.skipif(not OpenEyeToolkitWrapper.is_available(),
reason='OpenEye Toolkit not available')
def test_compute_wiberg_bond_orders(self):
"""Test OpenEyeToolkitWrapper compute_wiberg_bond_orders()"""
toolkit_wrapper = OpenEyeToolkitWrapper()
smiles = '[H]C([H])([H])C([H])([H])[H]'
molecule = toolkit_wrapper.from_smiles(smiles)
molecule.generate_conformers(toolkit_registry=toolkit_wrapper)
for charge_model in ['am1', 'pm3']:
molecule.compute_wiberg_bond_orders(
toolkit_registry=toolkit_wrapper, charge_model=charge_model)
print([bond.fractional_bond_order for bond in molecule.bonds])
# TODO: Add test for equivalent Wiberg orders for equivalent bonds
@pytest.mark.skipif(not OpenEyeToolkitWrapper.is_available(),
reason='OpenEye Toolkit not available')
def test_compute_wiberg_bond_orders_charged(self):
"""Test OpenEyeToolkitWrapper compute_wiberg_bond_orders() on a molecule with net charge +1"""
toolkit_wrapper = OpenEyeToolkitWrapper()
smiles = '[H]C([H])([H])[N+]([H])([H])[H]'
molecule = toolkit_wrapper.from_smiles(smiles)
molecule.generate_conformers(toolkit_registry=toolkit_wrapper)
for charge_model in ['am1', 'pm3']:
molecule.compute_wiberg_bond_orders(
toolkit_registry=toolkit_wrapper, charge_model=charge_model)
# TODO: Add test for equivalent Wiberg orders for equivalent bonds
@pytest.mark.skipif(not OpenEyeToolkitWrapper.is_available(),
reason='OpenEye Toolkit not available')
def test_compute_wiberg_bond_orders_double_bond(self):
"""Test OpenEyeToolkitWrapper compute_wiberg_bond_orders() on a molecule with a double bond"""
toolkit_wrapper = OpenEyeToolkitWrapper()
smiles = r'C\C(F)=C(/F)C[C@@](C)(Cl)Br'
molecule = toolkit_wrapper.from_smiles(smiles)
molecule.generate_conformers(toolkit_registry=toolkit_wrapper)
for charge_model in ['am1', 'pm3']:
molecule.compute_wiberg_bond_orders(
toolkit_registry=toolkit_wrapper, charge_model=charge_model)
# TODO: Add test for equivalent Wiberg orders for equivalent bonds
double_bond_has_wbo_near_2 = False
for bond in molecule.bonds:
if bond.bond_order == 2:
if 1.75 < bond.fractional_bond_order < 2.25:
double_bond_has_wbo_near_2 = True
assert double_bond_has_wbo_near_2